Thermomorphic fluorous phosphines as organocatalysts for Michael addition reactions

被引：8

作者：

Gimbert, Carolina ^{[1
]}

Vallribera, Adelina ^{[1
]}

Gladysz, John A. ^{[2
]}

Jurisch, Markus ^{[3
,4
]}

机构：

[1] Univ Autonoma Barcelona, Dept Chem, Cerdanyola Del Valles 08193, Spain

[2] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA

[3] Univ Erlangen Nurnberg, Inst Organ Chem, D-91054 Erlangen, Germany

[4] Univ Erlangen Nurnberg, Interdisciplinary Ctr Mol Mat, D-91054 Erlangen, Germany

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 35期

关键词：

ASYMMETRIC REDUCTION; CATALYSIS; SOLVENTS; IMINES;

D O I：

10.1016/j.tetlet.2010.06.136

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The fluorous phosphines P[(CH2)(m)R-fn](3) (R-fn = (CF2)(n-1)CF3; m/n = 2/8, 3/8, 3/10) are efficient nucleophilic catalysts of Michael addition reactions. They can be easily recycled based upon their highly temperature-dependent solubilities (thermomorphism), with recovery by simple liquid/solid phase separation. The phosphonium salt formed by reaction of the nucleophilic phosphine with the alpha,beta-unsaturated system appears to be a significant component of the catalyst rest state. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4662 / 4665

页数：4

共 30 条

[11] Michael additions catalyzed by phosphines.: An overlooked synthetic method [J].

Gimbert, C ;

Lumbierres, M ;

Marchi, C ;

Moreno-Mañas, M ;

Sebastián, RM ;

Vallribera, A .

TETRAHEDRON, 2005, 61 (36) :8598-8605

[12] Tributylphosphine, excellent organocatalyst for conjugate additions of non-nucleophilic N-containing compounds [J].

Gimbert, Carolina ;

Moreno-Manas, Marcial ;

Perez, Elisabet ;

Vallribera, Adelina .

TETRAHEDRON, 2007, 63 (34) :8305-8310

[13]

Gladysz JA., 2009, Handbook of green chemistry, vol 1: Homogeneous catalysis, V1, P17

[14]

GUNDMUNSEN D, 2009, J FLUORINE CHEM, V130, P942

[15] Solvents from nature [J].

Horvath, Istvan T. .

GREEN CHEMISTRY, 2008, 10 (10) :1024-1028

[16] FACILE CATALYST SEPARATION WITHOUT WATER - FLUOROUS BIPHASE HYDROFORMYLATION OF OLEFINS [J].

HORVATH, IT ;

RABAI, J .

SCIENCE, 1994, 266 (5182) :72-75

[17] The ying and yang of asymmetric aminocatalysis [J].

List, B .

CHEMICAL COMMUNICATIONS, 2006, (08) :819-824

[18] The advent and development of organocatalysis [J].

MacMillan, David W. C. .

NATURE, 2008, 455 (7211) :304-308

[19] Organocatalysis with a fluorous tag: Asymmetric reduction of imines with trichlorosilane catalyzed by amino acid-derived formamides [J].

Malkov, Andrei V. ;

Figlus, Marek ;

Stoncius, Sigitas ;

Kocovsky, Pavel .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1315-1325

[20] Asymmetric organocatalysis [J].

Pellissier, Helene .

TETRAHEDRON, 2007, 63 (38) :9267-9331

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